Disperse monoazo dyes derived from 3-aminodiphenylene oxides

ABSTRACT

DISPERSE DYES DERIVED FROM 3-AMINODIPHENYLENE OXIDES AND PYRAZOLONES FOR DYEING SYNTHETIC ORGANIC FIBERS SUCH AS CELLULOSE ESTER AND SYNTHETIC POLYESTER MATERIAL.

United States Patent 3,565,884 DISPERSE MONOAZO DYES DERIVED FROM 3-AMINODIPHENYLENE OXIDES Armin Haag, Grosssachsen, Germany, assignor to Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen (Rhine), Germany No Drawing. Filed Aug. 14, 1968, Ser. No. 752,456

Claims priority, application Germany, Aug. 16, 1967, P 16 44 065.6 Int. Cl. C09b 29/38; D06p N02 US. Cl. 260-162 3 Claims ABSTRACT OF THE DISCLOSURE Disperse dyes derived from 3-aminodiphenylene oxides and pyrazolones for dyeing synthetic organic fibers such as cellulose ester and synthetic polyester material.

This invention relates to disperse dyes having the For- HO-C Patented Feb. 23, 1971 ice and

with a pyrazolone having the general Formula III:

12 parts of 3-aminodiphenylene oxide is stirred in parts of water and 30 parts of concentrated hydrochloric acid for fifteen minutes. After parts of ice has been added, the amine is diazotized by adding 4.6 parts of sodium nitrite in a solution of 20 parts of Water at a temperature of from 0 to 5 C. The diazo solution is then coupled with a solution of 13.3 parts of l-phenylpyrazolone amide in 200 parts of 10% caustic soda solution and 100 parts of 5% sodium carbonate solution. When coupling is over at about 10 C., the whole is stirred for another hour, the reaction mixture is acidified slightly and the red dye is suction filtered. The yield is 24 parts having a melting point of 262 to 264 C. The very strong dye gives dyeings having good light fastness and excellent thermal stability on polyesters. The dye has the Formula e.

Dyes which give dyeings in the shades indicated on polyester fibers are obtained from the components set out in the following table by a method analogous to that of Example 1:

Amine Coupling component Shade Example:

NH N 2 I 5 Same as above H2=CCO O O C 11 Orange.

Yellow.

Red.

Amine Coupling component Shade Example:

7 Same as above H2=CC--CO O CzH Red.

O=C N If (EH5 8. Same as above Orange.

9 Same as above H2=(|3-fiC 0-NH2 Do.

O=C N i CoH5 I claim: in which Z and Y have the meanings given in claim 1. 1. A disperse dye having the formula: 3. The dye having the formula:

N=NOC-Z 0 g u HO- N N=N C CC O NH 0 2 References Cited UNITED STATES PATENTS 3,150,136 9/1964 Wolfrum et al. 260162X CHARLES B. PARKER, Primary Examiner D. M. PAPUGA, Assistant Examiner US. Cl. X.R. 841, 

